Identification of Penicillin G Metabolites under Various Environmental Conditions Using UHPLC-MS/MS

Abstract

In this work, we investigate the stability of penicillin G in various conditions including acidic, alkaline, natural acidic matrices and after treatment of citrus trees that are infected with citrus greening disease. The identification, confirmation, and quantitation of penicillin G and its various metabolites were evaluated using two UHPLC-MS/MS systems with variable capabilities (i.e., Thermo Q Exactive Orbitrap and Sciex 6500 QTrap). Our data show that under acidic and alkaline conditions, penicillin G at 100 ng/mL degrades quickly, with a determined half-life time of approximately 2 h. Penillic acid, penicilloic acid, and penilloic acid are found to be the most abundant metabolites of penicillin G. These major metabolites, along with isopenillic acid, are found when penicillin G is used for treatment of citrus greening infected trees. The findings of this study will provide insight regarding penicillin G residues in agricultural and biological applications.

Penicillin G's function, metabolites, allergy, and resistance.

“…Using the Orbitrap and triple-quadrupole based UHPLC-MS/MS platforms, we analyzed a citrus fruit sample taken from a HLB infected tree that was treated with penicillin G; the presence of the metabolites penillic acid, isopenillic acid, penilloic acid, and penicilloic acid were confirmed. Penicillin G was not found in the citrus sample, however this was anticipated, as environmental conditions on the growing field, such as heat, UV radiation, and acidic conditions of the fruit would contribute heavily to degradation after treatment [65,66].…”

“…This analytical technique is recognized for its exceptional specificity and selectivity, and its advantages were well suited to characterizing the degradation of penicillin G. Under acidic conditions, penicillin G is shown to have a rate of degradation of 0.29 h -1 corresponding to a half-life of 2.4 hrs at pH 2 when the concentration of penicillin G was 100 ng/mL. Penicillin G was not detectable after approximately 10-15 hours [65]. Our UHPLC-MS/MS analysis of penicillin G's degradation at pH 2 confirmed that penillic acid is the predominant species formed in acidic conditions, resulting in approximately 60% of the total metabolites ( Figure 3A).…”

“…Penicilloic acid is produced to some extent, resulting in almost 30% of the degradation products. The thiozolidine ring contained within penillic acid may rupture, forming isopenillic acid, which features a free thiol group [65]. Degradation in acidic media was of particular concern because if given orally, penicillin G would degrade tremendously in the stomach due to gastric acids.…”

Amount of Eurotium sp. in Chinese Liupao tea and its relationship with tea quality

“…However, a rapid and effective method for the simultaneous effective separation and rapid determination of anthraquinones, including emodin and physcion, in Liupao tea via UHPLC‐MS was developed and verified using HPLC. UHPLC‐MS is a rapid and effective method used in detecting various fungal metabolites (Natalia et al ; Aldeek et al ) and analysing agricultural residue in tea (Zhang et al ). The retention times of emodin and physcion in our method were 4·878 and 4·241 min, respectively.…”

Dual RNase and β-lactamase activity of a single enzyme encoded in most Archaea

“…As reported, penicillin G can be degraded in alkaline or acidic pH and in the presence of β-lactamase into different metabolites, including benzyl penilloic acid or benzylpenillic acid. A list of known chemical structures, including penicillin G and its metabolites (27, 28), were targeted with the following parameters: 0.1 minutes retention time window, 5 % CCS tolerance, 5 ppm m/z tolerance on parent adducts (H+ and Na+) and 10 mDa m/z tolerance on predicted fragments. Retention times and CCS values were previously measured from penicillin G degradation experiments at pH 2 and pH 10 in order to perform subsequent accurate structures screening.…”